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Convergent routes to substituted naphthylamides.

Ngoc Diem My Tran1, Samir Z Zard

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New synthetic methods create substituted naphthylamides using xanthate chemistry for radical additions and cyclizations. These practical routes offer efficient access to valuable chemical structures.

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Radical Chemistry

Background:

  • Naphthylamides are important structural motifs in medicinal chemistry and materials science.
  • Developing efficient and versatile synthetic routes to substituted naphthylamides remains a key challenge in organic synthesis.

Purpose of the Study:

  • To develop practical and convergent synthetic strategies for variously substituted 1- and 2-naphthylamides.
  • To explore the utility of xanthate chemistry in radical addition and cyclization reactions for constructing naphthylamide scaffolds.

Main Methods:

  • Utilizing xanthates to perform intermolecular radical additions to vinyl pivalate.
  • Employing intramolecular radical cyclizations onto aromatic rings.
  • Leveraging intramolecular hydrogen bonding to facilitate cyclization in 1-naphthylamide synthesis.

Main Results:

  • Successfully developed convergent synthetic routes to diverse 1- and 2-naphthylamides.
  • Demonstrated the effectiveness of xanthate-mediated radical reactions in constructing the target molecules.
  • Showcased the role of intramolecular hydrogen bonding in enhancing cyclization efficiency for 1-naphthylamides.

Conclusions:

  • The developed methods provide practical and efficient access to substituted naphthylamides.
  • Xanthate chemistry offers a versatile platform for radical-based synthesis of complex aromatic amides.
  • Intramolecular hydrogen bonding can be strategically employed to improve synthetic outcomes in related cyclization reactions.